PH26181A - Antidepressive substituted N-[{4-piperidinyl)alkyl] bicyclic condensed oxazol and thiazolamines - Google Patents
Antidepressive substituted N-[{4-piperidinyl)alkyl] bicyclic condensed oxazol and thiazolamines Download PDFInfo
- Publication number
- PH26181A PH26181A PH33642A PH33642A PH26181A PH 26181 A PH26181 A PH 26181A PH 33642 A PH33642 A PH 33642A PH 33642 A PH33642 A PH 33642A PH 26181 A PH26181 A PH 26181A
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- Philippines
- Prior art keywords
- hydrogen
- formula
- parts
- group
- methyl
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- 125000000217 alkyl group Chemical group 0.000 title claims abstract description 5
- 230000001430 anti-depressive effect Effects 0.000 title claims abstract description 5
- 125000002619 bicyclic group Chemical group 0.000 title abstract description 6
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 title abstract description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 26
- 239000002253 acid Substances 0.000 claims abstract description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 230000000648 anti-parkinson Effects 0.000 claims abstract description 5
- 239000000939 antiparkinson agent Substances 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 78
- 229910052739 hydrogen Inorganic materials 0.000 claims description 69
- 239000001257 hydrogen Substances 0.000 claims description 53
- -1 hydroxy, amino Chemical group 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 150000002431 hydrogen Chemical class 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- 241001465754 Metazoa Species 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000002541 furyl group Chemical group 0.000 claims description 10
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 230000003001 depressive effect Effects 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 238000007910 systemic administration Methods 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
- 229940125782 compound 2 Drugs 0.000 claims description 2
- 229940126214 compound 3 Drugs 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
- 240000002390 Pandanus odoratissimus Species 0.000 claims 1
- 235000005311 Pandanus odoratissimus Nutrition 0.000 claims 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 abstract description 8
- 230000000694 effects Effects 0.000 abstract description 4
- ONTLHMRTMPOOIY-UHFFFAOYSA-N 1,3-oxazole 1,3-thiazol-2-amine Chemical class C1=COC=N1.NC1=NC=CS1 ONTLHMRTMPOOIY-UHFFFAOYSA-N 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
- 239000000543 intermediate Substances 0.000 description 80
- 239000000203 mixture Substances 0.000 description 72
- 239000000243 solution Substances 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
- 239000000047 product Substances 0.000 description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
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- 239000003480 eluent Substances 0.000 description 24
- 150000003254 radicals Chemical class 0.000 description 24
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- 239000000284 extract Substances 0.000 description 19
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 18
- 238000007792 addition Methods 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 17
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 16
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 16
- 150000002540 isothiocyanates Chemical class 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000002585 base Substances 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
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- 238000003756 stirring Methods 0.000 description 13
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- 239000003054 catalyst Substances 0.000 description 12
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 12
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 11
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- 238000004440 column chromatography Methods 0.000 description 10
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- 125000005843 halogen group Chemical group 0.000 description 10
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 10
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- 150000004982 aromatic amines Chemical class 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
- 238000007126 N-alkylation reaction Methods 0.000 description 7
- 125000001309 chloro group Chemical group Cl* 0.000 description 7
- 230000028527 righting reflex Effects 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 6
- 238000010511 deprotection reaction Methods 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
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- 229960001600 xylazine Drugs 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
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- 239000002775 capsule Substances 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- IXRQNDCRKDYRJG-UHFFFAOYSA-N n-(piperidin-4-ylmethyl)-1,3-benzothiazol-2-amine;dihydrobromide Chemical compound Br.Br.N=1C2=CC=CC=C2SC=1NCC1CCNCC1 IXRQNDCRKDYRJG-UHFFFAOYSA-N 0.000 description 5
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- KCHXGUIOIGLIBD-UHFFFAOYSA-N 2-methylsulfanyl-[1,3]thiazolo[5,4-d]pyrimidin-7-amine Chemical compound N1=CN=C2SC(SC)=NC2=C1N KCHXGUIOIGLIBD-UHFFFAOYSA-N 0.000 description 4
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- PFCRYVSOQZMAOW-UHFFFAOYSA-N n-[2-[1-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)piperidin-4-yl]ethyl]-1,3-benzothiazol-2-amine Chemical compound C1=CC=C2SC(NCCC3CCN(CC4OC5=CC=CC=C5OC4)CC3)=NC2=C1 PFCRYVSOQZMAOW-UHFFFAOYSA-N 0.000 description 1
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- OXGZKUQHXJYZLD-UHFFFAOYSA-N n-methyl-n-(piperidin-4-ylmethyl)-1,3-benzothiazol-2-amine;dihydrobromide Chemical compound Br.Br.N=1C2=CC=CC=C2SC=1N(C)CC1CCNCC1 OXGZKUQHXJYZLD-UHFFFAOYSA-N 0.000 description 1
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
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- LTEKQAPRXFBRNN-UHFFFAOYSA-N piperidin-4-ylmethanamine Chemical compound NCC1CCNCC1 LTEKQAPRXFBRNN-UHFFFAOYSA-N 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
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- 239000004544 spot-on Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
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- 150000008163 sugars Chemical class 0.000 description 1
- NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical compound BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
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- 235000012431 wafers Nutrition 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Hydrogenated Pyridines (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72340085A | 1985-04-15 | 1985-04-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH26181A true PH26181A (en) | 1992-03-18 |
Family
ID=24906098
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH33642A PH26181A (en) | 1985-04-15 | 1986-04-14 | Antidepressive substituted N-[{4-piperidinyl)alkyl] bicyclic condensed oxazol and thiazolamines |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP0199400B1 (pt) |
| JP (1) | JPH08824B2 (pt) |
| KR (1) | KR930005004B1 (pt) |
| CN (1) | CN1019393B (pt) |
| AT (1) | ATE56972T1 (pt) |
| AU (1) | AU582642B2 (pt) |
| CA (1) | CA1271474A (pt) |
| DE (1) | DE3674448D1 (pt) |
| DK (1) | DK165183C (pt) |
| ES (1) | ES8702403A1 (pt) |
| FI (1) | FI82047C (pt) |
| GR (1) | GR861014B (pt) |
| HU (1) | HU196393B (pt) |
| IE (1) | IE59040B1 (pt) |
| IL (1) | IL78487A (pt) |
| NO (1) | NO163818C (pt) |
| NZ (1) | NZ215700A (pt) |
| PH (1) | PH26181A (pt) |
| PT (1) | PT82368B (pt) |
| SU (1) | SU1524809A3 (pt) |
| ZA (1) | ZA862776B (pt) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5120843A (en) * | 1987-04-27 | 1992-06-09 | Upjohn | Pharmaceutically active amines |
| IL90337A0 (en) * | 1988-05-24 | 1989-12-15 | Pfizer | Aromatic and heterocyclic carboxamide derivatives as antineoplastic agents |
| JP2679745B2 (ja) * | 1989-06-29 | 1997-11-19 | 明治製菓株式会社 | アゾール誘導体及びそれらを有効成分とする抗潰瘍剤 |
| US5089637A (en) * | 1990-03-21 | 1992-02-18 | Pfizer Inc. | Process and intermediates for 2r-benzyl-chroman-6-carbaldehyde |
| KR100190299B1 (ko) * | 1990-07-19 | 1999-06-01 | 디르크 반테 | 신규한 옥사졸릴 유도체 |
| FR2672888B1 (fr) * | 1991-02-14 | 1994-02-04 | Fabre Medicament Pierre | Nouvelles urees et thiourees, leur preparation et leur application en therapeutique. |
| ZW1992A1 (en) * | 1991-02-25 | 1993-09-22 | Janssen Pharmaceutica Nv | 4-/(2-benzotiazolyl)methylamino/-b-/(3,4-difluorephenoxy)methyl/-1-piperidine ethanol |
| DE4120322A1 (de) * | 1991-06-20 | 1992-12-24 | Bayer Ag | Aminomethyl-substituierte 2,3-dihydropyrano(2,3-b)pyridine, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
| AU4982293A (en) * | 1993-03-02 | 1994-09-26 | Fujisawa Pharmaceutical Co., Ltd. | Novel heterocyclic compound |
| TW282469B (pt) * | 1993-06-11 | 1996-08-01 | Janssen Pharmaceutica Nv | |
| FR2753970B1 (fr) * | 1996-10-01 | 1998-10-30 | Synthelabo | Derives de n-(benzothiazol-2-yl) piperidine-1-ethanamine, leur preparation et leur application en therapeutique |
| JP2000224822A (ja) | 1998-06-29 | 2000-08-11 | Mitsubishi Electric Corp | 電動パワーステアリング装置用モータ |
| KR100571161B1 (ko) * | 2000-06-21 | 2006-04-17 | 에프. 호프만-라 로슈 아게 | 벤조티아졸 유도체 |
| FR2821356A1 (fr) | 2001-02-23 | 2002-08-30 | Cerep | Nouveaux derives d'arylcarbamates et d'arylurees, preparations et utilisations |
| US7087761B2 (en) | 2003-01-07 | 2006-08-08 | Hoffmann-La Roche Inc. | Cyclization process for substituted benzothiazole derivatives |
| PL1753760T3 (pl) | 2004-05-24 | 2008-06-30 | Hoffmann La Roche | (4-metoksy-7-morffolin-4-ylobenzatiazol-2-ilo)amid kwasu 4-hydroksy-4-metylopiperydyno-1-karboksylowego |
| CA2586931C (en) | 2004-11-05 | 2013-08-06 | Paul Spurr | Process for preparation of isonicotinic acid derivatives |
| BRPI0609719B8 (pt) | 2005-03-23 | 2021-05-25 | Hoffmann La Roche | derivados de acetilenil-pirazol-pirimidina como antagonistas de mgbur2 |
| BRPI0616571A2 (pt) | 2005-09-27 | 2011-06-21 | Hoffmann La Roche | oxadiazolil pirazol-piridiminas como antagonistas de mglur2, processo para sua preparação, composição farmacêutica que os contém e uso dos mesmo |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4035369A (en) * | 1975-10-08 | 1977-07-12 | Janssen Pharmaceutica N.V. | 1-Benzazolylalkyl-4-substituted-piperidines |
| DE2545645C2 (de) * | 1975-10-11 | 1983-04-14 | Bayer Ag, 5090 Leverkusen | Thiazolinylamino-piperidin-Derivate |
| CA1140119A (en) * | 1978-04-03 | 1983-01-25 | Joseph Torremans | N-heterocyclyl-4-piperidinamines |
| PH23995A (en) * | 1984-01-09 | 1990-02-09 | Janssen Pharmaceutica Nv | 4((bicycle heterocyclyl)-methyl and hetero)piperidines |
| CA1260474A (en) * | 1984-12-03 | 1989-09-26 | Raymond A. Stokbroekx | Benzoxazol- and benzothiazolamine derivatives |
-
1986
- 1986-03-25 KR KR1019860002217A patent/KR930005004B1/ko not_active IP Right Cessation
- 1986-04-02 DE DE8686200552T patent/DE3674448D1/de not_active Expired - Fee Related
- 1986-04-02 EP EP86200552A patent/EP0199400B1/en not_active Expired - Lifetime
- 1986-04-02 AT AT86200552T patent/ATE56972T1/de not_active IP Right Cessation
- 1986-04-03 NZ NZ215700A patent/NZ215700A/xx unknown
- 1986-04-04 CA CA000505892A patent/CA1271474A/en not_active Expired - Fee Related
- 1986-04-07 JP JP61078429A patent/JPH08824B2/ja not_active Expired - Fee Related
- 1986-04-08 CN CN86102349A patent/CN1019393B/zh not_active Expired
- 1986-04-11 PT PT82368A patent/PT82368B/pt not_active IP Right Cessation
- 1986-04-11 ES ES553936A patent/ES8702403A1/es not_active Expired
- 1986-04-14 HU HU861560A patent/HU196393B/hu not_active IP Right Cessation
- 1986-04-14 PH PH33642A patent/PH26181A/en unknown
- 1986-04-14 ZA ZA862776A patent/ZA862776B/xx unknown
- 1986-04-14 DK DK169486A patent/DK165183C/da not_active IP Right Cessation
- 1986-04-14 SU SU864027244A patent/SU1524809A3/ru active
- 1986-04-14 IL IL78487A patent/IL78487A/xx not_active IP Right Cessation
- 1986-04-14 NO NO861442A patent/NO163818C/no not_active IP Right Cessation
- 1986-04-14 IE IE96786A patent/IE59040B1/en not_active IP Right Cessation
- 1986-04-14 FI FI861562A patent/FI82047C/fi not_active IP Right Cessation
- 1986-04-15 AU AU56135/86A patent/AU582642B2/en not_active Ceased
- 1986-04-16 GR GR861014A patent/GR861014B/el unknown
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